Sending EMail using SMTP with OAUTH

I have a few clients who have Hotmail, or Microsoft Live EMail accounts,

and these do not support the use of STARTTLS, to send EMails.

They do, however, support XOAUTH2.

I am using the EMan goodie to send EMails, and I have also been adding to that

goodie for the last few years.

Has anyone built an EMail client using OAUTH?

Any pointers, or a starting direction, would be greatly appreciated..

Thanks in advance....

And stay safe and healthy!

Regards,

Julian

Since 9.2, the mail application includes an authentication framework to implement SASL.
It supports CRAM-MD5, SCRAM-SHA-1, SCRAM-SHA-256, LOGIN, XOAUTH2 or a custom protocol you can define and hook into SASL.

Load the ST:Server Smalltalk (SST) - Mail (IMAP/SMTP) feature and review the SstMailAuthenticationApp for some idea.

If you want see how that looks from a protocol conversation standpoint...run some of the SstSmtpClientExample>>exampleSasl* examples which has logging enabled and prints these out to the Transcript.  You can then switch out the sasl authenticator used in the example with a SstSaslOAuth2Authenticator which requies a user and access token.

VAST just handles the SASL conversation and encoding for XOAUTH2...there are still specifics to understand with each provider (gmail, hotmail, yahoo...).

Of course, I know what we have in VAST is not EMan, but hopefully it may point you in the right direction.

-------------------------------------------------------------------------------------

Back to your original problem, you said that they don't support a STARTTLS upgrade.
But what about just an initial SSL connection?  If you login to their SSL/TLS port for Microsoft Live...what CAPABILITY listing does it answer?

- Seth

On Sunday, May 24, 2020 at 12:10:42 PM UTC-4, Julian Ford wrote:

Hello, all.

I have a few clients who have Hotmail, or Microsoft Live EMail accounts,

and these do not support the use of STARTTLS, to send EMails.

They do, however, support XOAUTH2.

I am using the EMan goodie to send EMails, and I have also been adding to that

goodie for the last few years.

Has anyone built an EMail client using OAUTH?

Any pointers, or a starting direction, would be greatly appreciated..

Thanks in advance....

And stay safe and healthy!

Regards,

Julian

- Seth

On Sunday, May 24, 2020 at 1:06:47 PM UTC-4, Seth Berman wrote:

Hi Julian,

Since 9.2, the mail application includes an authentication framework to implement SASL.
It supports CRAM-MD5, SCRAM-SHA-1, SCRAM-SHA-256, LOGIN, XOAUTH2 or a custom protocol you can define and hook into SASL.

Load the ST:Server Smalltalk (SST) - Mail (IMAP/SMTP) feature and review the SstMailAuthenticationApp for some idea.

If you want see how that looks from a protocol conversation standpoint...run some of the SstSmtpClientExample>>exampleSasl* examples which has logging enabled and prints these out to the Transcript.  You can then switch out the sasl authenticator used in the example with a SstSaslOAuth2Authenticator which requies a user and access token.

VAST just handles the SASL conversation and encoding for XOAUTH2...there are still specifics to understand with each provider (gmail, hotmail, yahoo...).

Of course, I know what we have in VAST is not EMan, but hopefully it may point you in the right direction.

-------------------------------------------------------------------------------------

Back to your original problem, you said that they don't support a STARTTLS upgrade.
But what about just an initial SSL connection?  If you login to their SSL/TLS port for Microsoft Live...what CAPABILITY listing does it answer?

- Seth

On Sunday, May 24, 2020 at 12:10:42 PM UTC-4, Julian Ford wrote:

Hello, all.

I have a few clients who have Hotmail, or Microsoft Live EMail accounts,

and these do not support the use of STARTTLS, to send EMails.

They do, however, support XOAUTH2.

I am using the EMan goodie to send EMails, and I have also been adding to that

goodie for the last few years.

Has anyone built an EMail client using OAUTH?

Any pointers, or a starting direction, would be greatly appreciated..

Thanks in advance....

And stay safe and healthy!

Regards,

Julian

I will try what you have suggested.

And yes, I am already using 9.2.1, so should have what I need.

Greatly appreciate the response!

Julian

On Sunday, May 24, 2020 at 1:08:16 PM UTC-4, Seth Berman wrote:

BTW, I would get 9.2.1 if you are going to experiment.
There were some SMTP fixes that were necessary for certain SMTP servers.

- Seth

On Sunday, May 24, 2020 at 1:06:47 PM UTC-4, Seth Berman wrote:

Hi Julian,

Since 9.2, the mail application includes an authentication framework to implement SASL.
It supports CRAM-MD5, SCRAM-SHA-1, SCRAM-SHA-256, LOGIN, XOAUTH2 or a custom protocol you can define and hook into SASL.

Load the ST:Server Smalltalk (SST) - Mail (IMAP/SMTP) feature and review the SstMailAuthenticationApp for some idea.

If you want see how that looks from a protocol conversation standpoint...run some of the SstSmtpClientExample>>exampleSasl* examples which has logging enabled and prints these out to the Transcript.  You can then switch out the sasl authenticator used in the example with a SstSaslOAuth2Authenticator which requies a user and access token.

VAST just handles the SASL conversation and encoding for XOAUTH2...there are still specifics to understand with each provider (gmail, hotmail, yahoo...).

Of course, I know what we have in VAST is not EMan, but hopefully it may point you in the right direction.

-------------------------------------------------------------------------------------

Back to your original problem, you said that they don't support a STARTTLS upgrade.
But what about just an initial SSL connection?  If you login to their SSL/TLS port for Microsoft Live...what CAPABILITY listing does it answer?

- Seth

On Sunday, May 24, 2020 at 12:10:42 PM UTC-4, Julian Ford wrote:

Hello, all.

I have a few clients who have Hotmail, or Microsoft Live EMail accounts,

and these do not support the use of STARTTLS, to send EMails.

They do, however, support XOAUTH2.

I am using the EMan goodie to send EMails, and I have also been adding to that

goodie for the last few years.

Has anyone built an EMail client using OAUTH?

Any pointers, or a starting direction, would be greatly appreciated..

Thanks in advance....

And stay safe and healthy!

Regards,

Julian

After the EHLO, the capabilities listing I receive is as follows:

On Sunday, May 24, 2020 at 1:06:47 PM UTC-4, Seth Berman wrote:

Hi Julian,

Since 9.2, the mail application includes an authentication framework to implement SASL.
It supports CRAM-MD5, SCRAM-SHA-1, SCRAM-SHA-256, LOGIN, XOAUTH2 or a custom protocol you can define and hook into SASL.

Load the ST:Server Smalltalk (SST) - Mail (IMAP/SMTP) feature and review the SstMailAuthenticationApp for some idea.

If you want see how that looks from a protocol conversation standpoint...run some of the SstSmtpClientExample>>exampleSasl* examples which has logging enabled and prints these out to the Transcript.  You can then switch out the sasl authenticator used in the example with a SstSaslOAuth2Authenticator which requies a user and access token.

VAST just handles the SASL conversation and encoding for XOAUTH2...there are still specifics to understand with each provider (gmail, hotmail, yahoo...).

Of course, I know what we have in VAST is not EMan, but hopefully it may point you in the right direction.

-------------------------------------------------------------------------------------

Back to your original problem, you said that they don't support a STARTTLS upgrade.
But what about just an initial SSL connection?  If you login to their SSL/TLS port for Microsoft Live...what CAPABILITY listing does it answer?

- Seth

On Sunday, May 24, 2020 at 12:10:42 PM UTC-4, Julian Ford wrote:

Hello, all.

I have a few clients who have Hotmail, or Microsoft Live EMail accounts,

and these do not support the use of STARTTLS, to send EMails.

They do, however, support XOAUTH2.

I am using the EMan goodie to send EMails, and I have also been adding to that

goodie for the last few years.

Has anyone built an EMail client using OAUTH?

Any pointers, or a starting direction, would be greatly appreciated..

Thanks in advance....

And stay safe and healthy!

Regards,

Julian

So it supports LOGIN?  Can you just use that?
@see SstSaslLoginAuthenticator

- Seth


On Sunday, May 24, 2020 at 4:48:26 PM UTC-4, Julian Ford wrote:

Sorry....missed the second part of your message....

After the EHLO, the capabilities listing I receive is as follows:

250-SIZE 157286400

250-PIPELINING

250-DSN

250-ENHANCEDSTATUSCODES

250-AUTH LOGIN XOAUTH2

250-8BITMIME

250-BINARYMIME

250-CHUNKING

250 SMTPUTF8

Julian

On Sunday, May 24, 2020 at 1:06:47 PM UTC-4, Seth Berman wrote:

Hi Julian,

Since 9.2, the mail application includes an authentication framework to implement SASL.
It supports CRAM-MD5, SCRAM-SHA-1, SCRAM-SHA-256, LOGIN, XOAUTH2 or a custom protocol you can define and hook into SASL.

Load the ST:Server Smalltalk (SST) - Mail (IMAP/SMTP) feature and review the SstMailAuthenticationApp for some idea.

If you want see how that looks from a protocol conversation standpoint...run some of the SstSmtpClientExample>>exampleSasl* examples which has logging enabled and prints these out to the Transcript.  You can then switch out the sasl authenticator used in the example with a SstSaslOAuth2Authenticator which requies a user and access token.

VAST just handles the SASL conversation and encoding for XOAUTH2...there are still specifics to understand with each provider (gmail, hotmail, yahoo...).

Of course, I know what we have in VAST is not EMan, but hopefully it may point you in the right direction.

-------------------------------------------------------------------------------------

Back to your original problem, you said that they don't support a STARTTLS upgrade.
But what about just an initial SSL connection?  If you login to their SSL/TLS port for Microsoft Live...what CAPABILITY listing does it answer?

- Seth

On Sunday, May 24, 2020 at 12:10:42 PM UTC-4, Julian Ford wrote:

Hello, all.

I have a few clients who have Hotmail, or Microsoft Live EMail accounts,

and these do not support the use of STARTTLS, to send EMails.

They do, however, support XOAUTH2.

I am using the EMan goodie to send EMails, and I have also been adding to that

goodie for the last few years.

Has anyone built an EMail client using OAUTH?

Any pointers, or a starting direction, would be greatly appreciated..

Thanks in advance....

And stay safe and healthy!

Regards,

Julian